Hexane → N-(4-tert-Butylbenzyl)-N-cyclopropyl-(3-isopropenylbenzyl)amine

HRID 1356837Notes

Reaction equation

HRID 1356837 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[C:12]([C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]([CH2:25][C:26]2[CH:27]=[C:28]([C:32](=O)[CH3:33])[CH:29]=[CH:30][CH:31]=2)[CH:22]2[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:12]([C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([CH3:1])=[CH2:33])[CH:27]=2)[CH:22]2[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8058HexaneHCID 185095303'-[N-(4-tert-Butylbenzyl)-N-cyclopropylaminomethyl]acetophenoneHCID 178418339Butyllithium

Product 1

HCID 18509396N-(4-tert-Butylbenzyl)-N-cyclopropyl-(3-isopropenylbenzyl)amineYield 35.2%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

The procedure described in Example 60 was repeated, except that methyl triphenylphosphonium bromide (0.32 g; 8.94×10−1 mmol), n-butyl lithium in n-hexane (1.56 M: 0.6 ml; 8.9×10−1 mmol), and Compound 82 (0.20 g; 5.96×10−1 mmol) were used, to thereby yield 0.07 g of the target compound (yield: 35.2%).

Sources & evidence

ORD record
ord-e16dfbd8cde7441ab5bf3681f7e2ace7
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

Loading…